JPH0527671B2 - - Google Patents
Info
- Publication number
- JPH0527671B2 JPH0527671B2 JP60004191A JP419185A JPH0527671B2 JP H0527671 B2 JPH0527671 B2 JP H0527671B2 JP 60004191 A JP60004191 A JP 60004191A JP 419185 A JP419185 A JP 419185A JP H0527671 B2 JPH0527671 B2 JP H0527671B2
- Authority
- JP
- Japan
- Prior art keywords
- quaternary ammonium
- weight
- amine
- amount
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 ether amine Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 23
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 17
- 229940008406 diethyl sulfate Drugs 0.000 claims description 14
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 13
- 238000005956 quaternization reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000047 product Substances 0.000 description 31
- 239000002216 antistatic agent Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000835 fiber Substances 0.000 description 8
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910003953 H3PO2 Inorganic materials 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/571,038 US4540521A (en) | 1984-01-16 | 1984-01-16 | Liquid quaternary ammonium antistatic compositions |
| US571038 | 2000-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60161477A JPS60161477A (ja) | 1985-08-23 |
| JPH0527671B2 true JPH0527671B2 (xx) | 1993-04-21 |
Family
ID=24282072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60004191A Granted JPS60161477A (ja) | 1984-01-16 | 1985-01-16 | 改良された液体の第四級アンモニウム静電防止組成物 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4540521A (xx) |
| JP (1) | JPS60161477A (xx) |
| DE (1) | DE3501293A1 (xx) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210829B1 (en) * | 1985-07-22 | 1989-11-02 | Honda Giken Kogyo Kabushiki Kaisha | Exhaust timing control apparatus |
| DE3668348D1 (de) * | 1985-07-22 | 1990-02-22 | Honda Motor Co Ltd | Vorrichtung zur steuerung der auslasszeit einer brennkraftmaschine. |
| CA2001401A1 (en) * | 1988-10-25 | 1990-04-25 | Claude Piantadosi | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
| US4904825A (en) * | 1988-11-08 | 1990-02-27 | Ppg Industries, Inc. | Quaternary ammonium antistatic compounds |
| US5187214A (en) * | 1988-11-08 | 1993-02-16 | Ppg Industries, Inc. | Quaternary ammonium antistatic polymer compositions |
| US5053531A (en) * | 1988-11-08 | 1991-10-01 | Ppg Industries, Inc. | Quaternary ammonium antistatic compounds |
| US5173033A (en) * | 1990-12-11 | 1992-12-22 | Adahan Inc. | One-way umbrella valve and portable fluid pumping device including same |
| US5462912A (en) * | 1991-10-09 | 1995-10-31 | Kao Corporation | Agricultural chemical composition enhancer comprising quaternary di(polyoxyalkylene) ammonium alkyl sulfates |
| DE69431596T4 (de) * | 1993-06-10 | 2003-10-30 | University Of North Carolina At Chapel Hill, Chapel Hill | (phospho)lipide zum bekämpfen einer hepatitis b-infektion |
| JP4259611B2 (ja) * | 1994-08-29 | 2009-04-30 | ウェイク フォレスト ユニバーシティ | ウィルス感染を治療するための脂質アナログ |
| US7135584B2 (en) * | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| US7026469B2 (en) * | 2000-10-19 | 2006-04-11 | Wake Forest University School Of Medicine | Compositions and methods of double-targeting virus infections and cancer cells |
| US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
| WO2002096826A2 (en) * | 2001-05-29 | 2002-12-05 | Koninklijke Philips Electronics N.V. | Metal-ceramic bond |
| MXPA04001917A (es) * | 2001-08-31 | 2004-06-15 | Thomson Licensing Sa | Contador de secuencia para una corriente audio-visual. |
| DE10327026B4 (de) * | 2003-06-16 | 2010-11-04 | Hakle-Kimberly Deutschland Gmbh | Airlaidverfahren mit verbessertem Durchsatz, Faservlies, Verwendung einer Viskosekurzfaser und Absorbierender Gegenstand |
| US20050187191A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Louis S. | Methods and compositions for the treatment of respiratory syncytial virus |
| US7935222B2 (en) * | 2005-03-04 | 2011-05-03 | Kemira Chemicals, Inc. | Papermaking method using one or more quaternized dialkanolamine fatty acid ester compounds to control opacity and paper product made thereby |
| CN116003282B (zh) * | 2022-12-31 | 2024-03-05 | 杭州瑞思新材料有限公司 | 一种抗静电剂的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113956A (en) * | 1960-03-07 | 1963-12-10 | Robinette Res Lab Inc | Low viscosity quaternary ammonium ethosulfate compositions and methods |
| US3141905A (en) * | 1963-04-29 | 1964-07-21 | Witco Chemical Corp | Cation-active surface active quaternary ammonium compounds |
| GB1084134A (en) * | 1964-07-14 | 1967-09-20 | Mafchon Products Ltd | Novel quaternary ammonium salts, their preparation and use as surface-active agents |
| US3517045A (en) * | 1968-06-07 | 1970-06-23 | American Cyanamid Co | Hydroxyalkyl quaternary ammonium ethers as antistatic agents |
| DE1802807C3 (de) * | 1968-10-12 | 1973-11-08 | Chemische Werke Huels Ag, 4370 Marl | Antielektrostatische Polyolefine |
| JPS5010439B2 (xx) * | 1971-11-15 | 1975-04-21 | ||
| US3914496A (en) * | 1974-03-01 | 1975-10-21 | Basf Ag | Antistatic finishing of surfaces |
| DE2651898A1 (de) * | 1976-11-13 | 1978-05-18 | Hoechst Ag | Waescheweichspuelmittel |
| DE2843659C3 (de) * | 1978-10-06 | 1984-05-24 | Hoechst Ag, 6230 Frankfurt | Verwendung quaternierter Etheramine als Faserpräparationsmittel |
| DE3263800D1 (en) * | 1981-01-16 | 1985-07-04 | Procter & Gamble | Textile treatment compositions |
-
1984
- 1984-01-16 US US06/571,038 patent/US4540521A/en not_active Expired - Lifetime
-
1985
- 1985-01-16 JP JP60004191A patent/JPS60161477A/ja active Granted
- 1985-01-16 DE DE19853501293 patent/DE3501293A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4540521A (en) | 1985-09-10 |
| DE3501293A1 (de) | 1985-08-22 |
| JPS60161477A (ja) | 1985-08-23 |
| DE3501293C2 (xx) | 1993-07-08 |
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